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In an article in the Radio Times in January 2011, Webb revealed that his natural father was Peter Woods who was formerly a reporter with the Daily Mirror and later became a BBC newsreader.[4] Woods was married and Webb's mother, then Gloria Crocombe, was a secretary at the Daily Mirror and was divorced from her first husband at the time of the affair with Woods.[5] Webb commented that his mother's split from Woods may have been as much her doing as his, saying "I do not believe she was abandoned".[4] Woods provided financially for Webb but saw his son only once, when he was six months old.[6] Webb took the surname of his stepfather when his mother remarried in 1964.[1]

Webb joined the BBC as a graduate trainee in 1984 working in Northern Ireland for BBC Radio Ulster based in Belfast. He then worked as a reporter for BBC Radio 4's Today programme, before becoming a foreign affairs correspondent based in London and covering news around the world. He reported on the Gulf War and the war in Bosnia, the collapse of the Soviet Union and the first democratic elections in South Africa.

In 2001, Webb moved to the United States, as the BBC's chief Washington correspondent.[8] Much of his time was spent on local Washington Radio, most notably, WAMU, a public radio station, on The Diane Rehm Show. He raised eyebrows within the BBC in 2006 when, at a seminar on impartiality, he claimed the corporation was anti-American and treated the US with "scorn and derision", according it "no moral weight".[9] He has also presented a Radio 4 series on anti-Americanism.[10] In December 2007, he became North American Editor for BBC News, a role newly created in time for the American presidential election of 2008.[11] He replaced Matt Frei who moved to present the new World News America bulletin. Since November 2007, Webb has maintained a regularly updated blog on the BBC website.

In August 2009, he returned to the UK to replace Edward Stourton on the Today programme.[3]

In August 2009, Webb returned to the UK with his wife Sarah and their three children. Whilst in the United States, his son Sam fell ill and was diagnosed with type 1 diabetes mellitus. As a result, Webb experienced the United States healthcare system first-hand. His son commonly joins his father in speaking about the disease. In 2012, Webb joined son Sam at Addenbrooke's Hospital in Cambridge, meeting the Duchess of Cornwall as she visited the facilities. She later became a Royal Patron of the children's charity, JDRF, a charity which Webb supports on a regular basis.[12]